Nitrosobenzene → (E)-N-hydroxy-2-methyl-N,3-diphenylacrylamide

HRID 1099338Notes

Reaction equation

HRID 1099338 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12]/[C:13](=[CH:16]\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)/[CH:14]=[O:15].[N:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>ClCCl>[OH:24][N:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14](=[O:15])/[C:13](/[CH3:12])=[CH:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11473NitrosobenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5372813alpha-METHYLCINNAMALDEHYDE

Product 1

HCID 25115717(E)-N-hydroxy-2-methyl-N,3-diphenylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (15 mg, 0.1 mmol) was added under argon to a solution of (E)-2-methyl-3-phenylacrylaldehyde (146 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (36.4 mg, 0.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-3c3bd15da93b4e7485fed6a1e075a7de
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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